Isolation and antifungal activity of 4-phenyl-3-butenoic acid from Streptomyces koyangensis strain VK-A60

J Agric Food Chem. 2005 Oct 5;53(20):7696-700. doi: 10.1021/jf050957r.

Abstract

An antifungal compound was isolated from the culture broth of Streptomyces koyangensis strain VK-A60 using various chromatographic procedures. On the basis of the high-resolution EI-mass and 1H and 13C NMR data, the compound was identified as 4-phenyl-3-butenoic acid. Colletotrichum orbiculare, Magnaporthe grisea, and Pythium ultimum were most sensitive to 4-phenyl-3-butenoic acid. Strong inhibitory effects of 4-phenyl-3-butenoic acid also were found against Pectobacterium carotovorum subsp. carotovorum and Ralstonia solanacearum. 4-Phenyl-3-butenoic acid effectively suppressed the development of M. grisea on rice leaves at the concentration of more than 10 microg/mL, and the protective activity was in general similar to that of the commercial fungicide tricyclazole. Treatment with 100 microg/mL of 4-phenyl-3-butenoic acid also effectively inhibited the anthracnose development on cucumber plants, although its in vivo efficacy was somewhat less effective than that of the commercial fungicide chlorothalonil.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Culture Media, Conditioned / chemistry
  • Fatty Acids, Monounsaturated / isolation & purification*
  • Fatty Acids, Monounsaturated / pharmacology*
  • Fungi / drug effects
  • Fungicides, Industrial / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Streptomyces / metabolism*

Substances

  • Culture Media, Conditioned
  • Fatty Acids, Monounsaturated
  • Fungicides, Industrial
  • 4-phenyl-3-butenoic acid